CS246432B1 - Cationic esteramines - Google Patents

Abstract

The solution concerns the canonical esteramines of the general formula k© k [R1NHR2NHR3] ——X where k represents an integer of 1 to 4 n an integer of 1, 2 or 3 Ri residue, k o structure R4OOCCHCH2COOR4 R2 residue o structure — (CH2CH2NH j mCH2CH2— R3 hydrogen atom or Ri R4 alkyl with 4 to 8 carbon atoms m integer 1, 2 or 3 and X anion of a strong organic or inorganic acid. Substances (are suitable as lubricants for the surface treatment of glass fibers.

Description

The invention relates to cationic esteramines suitable for surface treatment of glass fibers.

The use of direct lubricants is known in the art for treating glass fibers used as reinforcing plastics. This method brings with it a number of problems with the selection of lubricants.

In the case of the application of the fibers as reinforcement of polar thermoplastics, it is necessary for a good wetting of the fibers with a polymer to be provided with a polar coating, mainly based on nitrogenous substances. For these reasons, aliphatic polyamine-based compounds, generally modified with epoxy or carboxyl derivatives, are constantly in the spotlight.

In this way, water-soluble amines or emulsifiable are obtained by converting them into salts of water-soluble acids. While it is possible to prepare suitable lubricating compounds using fatty acid glycidyl esters, the main drawback is the need to prepare glycidyl esters of fatty acids which are not commercially available and, last but not least, the lack of basic fatty acids.

These disadvantages are overcome in the manufacture of the modified aliphatic polyamines of the invention.

The present invention provides cationic esteramines of the general formula k where R 1 is an integer of 1, 2 or 3 R 1 is a radical of structure

R 3 is hydrogen or R 1

R 4 is C 4 -C 8 alkyl having an integer of 1, 2 or 3; and X anion of a strong organic or inorganic acid.

The preparation of these compounds can be carried out by treating aliphatic polyamines such as diethylenetriamine, triethylenetetramine and tetraethylenepentamine with the corresponding dialkyl esters of butenidic acid with a linear or branched alkyl such as n-butyl, pentyl, hexyl, heptyl, octyl and 2-ethylhexyl 1: as a result of neutralizing acids such as hydrochloric, phosphoric, acetic and the like.

The advantage of this process is the easy availability of raw materials that are readily available and low labor and equipment requirements. From these reasons, their production is also feasible in companies not involved in immediate chemical production.

The invention is further illustrated by way of examples.

Example 1

Preparation of esteramines of the formula to [CH3 (CH2) 3OOCCHNHCH2CH2 CH3 (CH2) 3OOC CH2

NH. to OOCCH3

R4OOCCHCH2COOR4

R 2 - (CH 2 CH 2 NH) _m CH 2 CH 2 -

Table 1

Acid to Mol. weight (g) knife (g.mol ^-1 )

300 g (1.3 mol) of dibutyl maleate were added to the flask. It was added with stirring

67.1 g (0.65 mol) of diethylenetriamine. The exotherm of the batch temperature rose to 90 ° C and held at 100 ° C for 1.5 h. Acetic acid was added to 100 g of the esteramine thus prepared and after homogenization at 30 ° C the batch was cooled. The amount of acid and the properties of the cationic esteramines at 20 degrees C are shown in Table 1.

Viscosity Density n _D ²⁰ (mPa.s) (kg.m ^-3 )

10.7 1 619.79 315.9 1071 1.4644 21.4 2 679.84 375.1 1081 1.4602 32.1 3 739.89 400.3 1087 1.4579

Example 2

Preparation of esteramines of formula

IR4OOCCHNHCH2CH2 Iwoc CH2 ©

NH. 3 OOCCH3

80 g of the appropriate dialkyl maleate and diethylenetriamine were charged to the flask. The batch was held at 100 ° C for 1.5 h. When the temperature dropped to 30 ° C, it was neutralized with acetic acid. Amine amounts, acids and properties are shown in Table 3.

248432

Table 3

R4 Amin (G) acid (G) Mol. weight (g. mol ^-1 ) n _D ²⁰ pentyl 16.1 28.1 796.00 1.4532 n-hexyl 14.5 25.3 852.13 1.4546 n-heptyl 13.2 23.1 908.22 1.4553 n-octyl 12.1 21.2 964.33 1.4551 2-ethylhexyl 12.1 21.2 964.33 1.4562

The effect of salts on reducing the surface tension of water at 20 ° C is shown in Table 4.

Table 4

R3 Concentration Surface tension (gl ^-1 ) (mN.nr ¹ )

pentyl 0,5 1 32.3 29.3 n-hexyl 0,5 1 39.2 36.8 n-heptyl 0,5 1 48.5 36.4 n-octyl 0,5 1 45.5 33.3 2-ethylhexyl 0,5 1 38.4 35.4

Example 3

Preparation of esteramines of formula

C4H9OOCCHNHC2H4NHC2H4NHC2H4NHCHCOOH9C4

C4H9OOC CH2

CH2COOH9C4

. 4X ©

200 g (0.88 mol) of dihutyl maleate and 64 g (0.44 mol) of triethylemetretramine were charged to the flask. The batch temperature was maintained at 90 ° C for 2 h. After the temperature dropped to 30 ° C, acid was added to 50 g of the esteramine with stirring. The amount of acid and the properties of the cationic esteramines are shown in Table 5.

Table 5 Acid

Quantity Mol. mass n _D ²⁰ (g) (g. mol ^-1 ) form 15,3 hydrochloric (37%) 32,7

Example 4

Preparation of esteramines of formula

C4H9OOC — CHNHC2H4NHC2H4 NH. H3PO4 C4H9OOC-CH2 J

Table 6 (gl ¹ ) 2 - (mN.m ^-1 ) 36.4

786.90 1.4727

784.62 1.4652

50 g (0.22 mol) of dihutyl maleate and 20.7 g (0.11 mol) of tetraethylenepenitamine were charged to the flask. The batch temperature was maintained at 90 ° C for 2 h. When the temperature dropped to 30 ° C, it was neutralized by homogenization with 12.6 g of 85% phosphoric acid) and diluted with water to a 50% solution on _D ²⁰ = 1.3972. The effect of this salt solution on the reduced surface tension of water is shown in Table 6.

6 10

34.4 33.3 33.3

Example 5

Preparation of esteramines of formula

R4 — OOC — CH — NH — CH2 — CH2 — NH — CH2 — CH2 — NH2 → OOCCH3

R4-OOC-CH2

100 g of dialkyl maleate and diethylenetriamine were charged to the flask. The batch temperature was maintained at 90 ° C for 1 h. Po ^; When the temperature dropped to 30 ° C, the batch was mixed with acid

R4 Aminic acid (gl- (g) n-butyl 45.2 26.3)

2-ethylhexyl 30.3 17.6 vinegar. The amounts of acid, diethylenetriamine, and the properties of the cationic esteramines at 20 ° C are shown in Table 7.

Viscosity Density n _D ^Z0 (mPa.s) (kg.m ^-3 )

306 1114 1.4747

276 1012 1.4699

Claims (1)

246432 1 100 g of dialkylmintinate and diethylenetriamine were introduced into the flask. The batch temperature was maintained for 1 h at 90 ° C. After; the drop of 30 ° C was mixed with the acid. Table 7 R 4 Amine Acid (g) (g) n-butyl 45.2 26.3 2-ethylhexyl 30.3 17.6 acetic acid, amount of acid, diethylenetriamine and properties cationic esteramines at 20 ° C are shown in Table 7. Viscosity Density nDZ0 (mPa.s) (kg.m-3) 5 306 1114 1.4747 2 276 1012 1.4699 OBJECT Cationic esteramines of the formula k® kn® [R1NHR2NHR5] - X wherein k is an integer from 1 to 4n an integer of 1, 2 or 3 ynAlez Rt residue having the structure R4OOCCHCH2COOR4R2 residue having the structure - (CH2GH2NH UCH2CH2 - R3 hydrogen atom or R1R4 alkyl having 4 to 8 carbon atoms integer 1, 2 or 3 aX strong organic anion or inorganic acid Severogratla, np, 7, Most Price 2,40 Kčs